US3685955A - Synthetic fiber dyeing with hexamethyl phosphoric acid triamide and chlorinated ethylene solution of disperse dye - Google Patents

Synthetic fiber dyeing with hexamethyl phosphoric acid triamide and chlorinated ethylene solution of disperse dye Download PDF

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Publication number
US3685955A
US3685955A US881623A US3685955DA US3685955A US 3685955 A US3685955 A US 3685955A US 881623 A US881623 A US 881623A US 3685955D A US3685955D A US 3685955DA US 3685955 A US3685955 A US 3685955A
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United States
Prior art keywords
dyeing
phosphoric acid
dyestuffs
acid triamide
fibre
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Expired - Lifetime
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US881623A
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English (en)
Inventor
Branimir Milicevic
Alfred Litzler
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Novartis AG
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Ciba Geigy AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/667—Organo-phosphorus compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
    • D06P1/924—Halogenated hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/921—Cellulose ester or ether
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • polyester fibres are difficult to dye with conventional aqueous dyestulf dispersions because of their compact hydrophobic nature.
  • Polyester fibres must therefore be dyed either in the presence of so-called carriers or in costly pressure vats which may require a dyeing time of several hours.
  • the possibility of dyeing linear polyester fibres is also considerably influenced by their degree of crystallinity.
  • So-called textured fibres in which the fibre structure has been subsequently changed by a physical treatment, for example to produce a crimp effect, have varying degrees of crystallinity and it is thus very difficult to obtain even dyeings.
  • the present invention is based on the observation that commercial textile material of hydrophobic fully synthetic fibres, filaments, as Well as yarns and knitted and woven fabrics made therefrom, especially those based on polyesters and nylon filaments, can be successfully dyed by replacing the usual aqueous liquor in which the dye 'ice stuif is dispersed by a solution of the dyestuff in an organic solvent mixture.
  • polyester fibres or filaments having an especially 7 low degree of crystallinity such as are obtained at an intermediate stage in the manufacture of polyester fibres, but it could not be foreseen that fully stretched commercial polyester fibres of a higher degree of crystallinity, ready for weaving, could also be dyed in a satisfactory manner in the presence of high-boiling organic solvents.
  • dimethylsulproxide has already been proposed as an organic solvent for dyeing hydrophobic fibres, but with this solvent the dyeings produced on polyester fabrics are not level.
  • solvent mixtures have been proposed for dyeing polyester materials, but these solvents contain a flammable ingredient.
  • hydrophobic fibres can be dyed with a mixture of a disperse dyestuff and a liquid or pasty dispersant which, if desired, may contain aliphatic alcohols, but these dispersants are not solvents in the usual sense.
  • One advantage of the use of organic solvents as dyeing media is that the dyed material is much more level, the dyeing all over the fabric being particularly more uniform.
  • the present process has the advantage that a smaller quantity of waste water is produced in the dyeing process.
  • Another advantage of the process of this invention compared with the conventional dyeing with aqueous dispersions of the dyestuffs is that it can be performed with the use of unconditioned dyestuffs, whereas in conventional dyeing processes from an aqueous dyebath it is always necessary to use specially conditioned dyestuff preparations to facilitate their dispersion in water.
  • dyestuffs can be used that have been found to be unsuitable for dyeing in conventional processes from an aqueous medium.
  • the range of suitable dyestuflis is widened by dyeing from solvents.
  • the present invention provides a process for dyeing textile material made of hydrophobic polymers containing polar groups, ready for weaving, especially of linear polyesters and polyamides, wherein the textile material is impregnated or printed, preferably padded, with a solution of at least one dyestuff in a mixture of a hydrophobic solvent and up to 50% of a phosphorus compound containing oxygen, especially an alkylated phosphoric acid triamide, whereupon the dyestutf is fixed on the textile material fibre by subjecting the latter to a heat treatment, preferably a treatment with dry heat, at a temperature below the softening point of the fibrous material.
  • a heat treatment preferably a treatment with dry heat
  • the present dyeing process can be applied to any type of hydrophobic fibre containing polar groups, for example cellulose 2 /2-acetate and triacetate fibres, acrylonitrile polymers and copolymers and especially polyester fibres and polyamide fibers.
  • polar groups for example cellulose 2 /2-acetate and triacetate fibres, acrylonitrile polymers and copolymers and especially polyester fibres and polyamide fibers.
  • Polyolefine fibres free from polar groups are not included in fibres suitable for dyeing by the present process.
  • the preferred material to be dyed according to the present process is textile material made of aromatic polyesters, for example polyesters of terephthalic acid and ethylene glycol or 1,4-dimethylolcyclohexane, or copolymers of terephthalic or isophthalic acid and ethylene glycol.
  • the present dyeing process is also specially suitable for all synthetic polyamides, more especially poly-(hexamethylene-adipamide) or nylon 66, or poly-(e-caprolactam) or nylon 6, poly-(hexamethylene-sebacic acid amide) or nylon 610 and poly-( l l-aminoundecanoic acid) or nylon 11.
  • the process of this invention yields especially good results in dyeing filament fabrics.
  • hydrophobic solvents used in accordance with the invention must also be inert towards the fibres or filaments at the dyeing temperature; acetophenone or, if desired, halogenated hydrocarbons for example chlorobenzene and preferably aliphatic hydrocarbons for example, carbon tetrachloride, chloroform, methylene chlo ride, trichloroethylene, perchlorethylene, trichlorethane or dibromoethylene may be used.
  • Suitable phosphorus compounds containing oxygen are the dialkylphosphites for example dimethylphosphite or ethylphosphite, and the derivatives of phosphoric acid, G 5 )a 2 5 )3 (C6H5S)3PO 3 3)2 and more especially the hexaalkyl-phosphoric acid amides for example hexaethyl-phosphoric acid amide and preferably the hexamethyl-phosphoric acid triamide of the formula OP[N(CH
  • liquid tensides that is to say liquids that contain a hydrophilic and a hydrophobic residue in one and the same molecule, are not covered by the term hydrophobic solvents, even when they are capable of dissolving the dyestuffs.
  • a simple small-scale test may be made before proceeding with the dyeing to ascertain whether the fibre remains undissolved under the dyeing conditions in the presence of the solvent. If necessary, the time of contact between the solvent and the fibre may be shortened to prevent a major attack on the fibre, or a higher proportion of chlorinated hydrocarbons can be used.
  • dyestuffs are suitable for use in the present dyeing process: monoazo and disazo dyestuffs, anthraquinone, naphthoperinone, quinophthalone, oxazine, phthalocyanine and methine dyestuffs, including the styryl, azamethine and azostryryl dyestuffs; metal complex compounds of the azo and formazan dyestuffs. Representatives of other suitable structural types may likewise be used.
  • dyestuffs are specially suitable: water-soluble acid dyestuffs, including acid levelling dyestuffs which can be used for dyeing either in the presence of acetic or formic acid or in a neutral medium until the aqueous dyebath is exhausted; pre-metallized dyestuffs having a ratio of metal to dyestuff of 1:1 or 1:2, which may but need not contain groups imparting solubility in water; metal-free dyestuffs not containing groups imparting solubility in water (listed in the Colour Index as Solvent Dyes) which are soluble in ketones, esters, alcohols or aromatic solvents, and other organic dyestuffs free from groups imparting solubility in water, especially the so-called disperse dyestuffs defined in the Colour Index.
  • acid levelling dyestuffs which can be used for dyeing either in the presence of acetic or formic acid or in a neutral medium until the aqueous dyebath is exhausted
  • pre-metallized dyestuffs having a ratio of
  • Vat dyestuffs in the unreduced state insofar as they are soluble in one of the solvents mentioned above are more especially suitable for polyester fibres.
  • the said dyestuffs are chosen according to their suitability for the individual type of fibre to be dyed.
  • Polyester fibres are preferably dyed with disperse dyestuffs and polyamide fibres with water-soluble fibre-reactive dyestuffs or preferably with fibre-reactive disperse dyestufls.
  • the present process is preferably performed without addition of dispersants; this offers the advantage that the dyed textile material is easier to clean. But, if desired, non-ionic emulsifiers may be added to the dyebath or padding liquor, preferably in an amount not exceeding 40%.
  • Ethers of polyhydroxy compounds for example polyoxyalkylated fat alcohols, polyoxyalkylated polyols, polyoxyalkylated mercaptans and aliphatic amines, polyoxyalkylated alkyl-phenols and -naphthols, polyoxyalkylated alkylarylmercaptans and alkylarylamines;
  • fatty acid esters of the ethylene glycols and polyethylene glycols as well as those of propylene glycol and butylene glycol, glycerol or polyglycerols and pentaerythritol, sugar alcohols for example sorbitol, sorbitans and saccharose;
  • emulsifiers in these groups are for example: adducts of 8 mols of ethylene oxide and 1 mol of para-tertiary octylphenol, 15 or 6 mols of ethylene oxide and caster oil, or 20 mols of ethylene oxide and the alcohol C H OH; adducts of ethylene oxide and di-(a-phenylethyl)phenols; polyethylene oxide-tertiary dodecyl thioether; polyamine-polyglycol ether or adducts of 15 or 30 mols of ethylene oxide and 1 mol of the amine C H NH or C H NH, or liquid polyethylene glycols.
  • the dyebath may further contain thickeners, for example cellulose esters or others, and also carriers.
  • any undissolved matter may be removed from the dyestuff solution by mechanical operations, for example filtration or centrifugation.
  • Padding is performed either at room temperature or with heating. After having been conveyed through the dyestuff solution the textile material is squeezed to the desired content of about 20 to 130% of impregnating solution referred to the weight of the dry fibre.
  • the impregnated or printed material leaving the padder or the printing machine is freed from the bulk of the adhering dyestuff solution by drying for a short time in a current of air heated, for example at 30 to C., or in another way, for example by centrifuging, or it is subjected to the fixing or thermofixation as it is. This is carried out at a temperature above C. preferably at a temperature of at least to 240 C. In any case the temperature during the fixing must not reach the softening temperature of the fibre.
  • the heat-setting is performed, for example, by steaming or preferably by a dry-heat treatment, for example by contact heat, treatment with a high frequency alternating current or infra-red irradiation.
  • the optimum conditions for the heat-setting treatment without damage to the fibre can be determined by means of a simple preliminary experiment.
  • EXAMPLE 1 A safety belt made of polyester is padded in the cold with a solution of 9 parts of the dyestuff of the formula described in Swiss Pat. 439,526
  • a yellow dyeing fast to light and washing is obtained having a fastness to rubbing value of 4 to without any after-cleaning.
  • the resulting blue dyeing has properties similar to those mentioned in Example 4.
  • NH-CHa are dissolved in 100 parts of hexamethylphosphoric acid triamide as described in Example 7 and diluted with per- 0 chloroethylene to 1000 parts. This liquor is used to dye a cellulose 2 /2-acetate fabric. The increase in Weight is about 50%. The fabric is intermediately dried and then heated for to seconds at 120 C. The after-treatment is carried out as in Example 7. A brilliant yellow dyeing is obtained.
  • EXAMPLE 9 in 1000 parts of a mixture consisting of 940 parts of perchloroethylene and 60 parts of hexamethylphosphoric acid triamide, squeezed to a weight increase of 60%, dried in a current of air heated at 40 to 50 C. and finally heattreated for 90 seconds at 200 C.
  • the dyeing is aftertreated as described in Example 7, but it is soaped at 80 C. A strong yellow dyeing is obtained which is fast to light and washing.
  • a process for dyeing linear polyester, polyamide, cellulose acetate or acrylic fibers comprising applying to said fibers a solution of a disperse dyestutf in a mixture of a chlorinated ethylene and up to 50% of hexamethyl phosphoric acid triamide, drying the fiber and then heating the fiber to at least C. and below the softening point of the fiber for a short period of time.
  • a process according to claim 1 which comprises printiirijg linear polyester, polyamide, cellulose acetate or acrylic ers.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US881623A 1968-12-05 1969-12-02 Synthetic fiber dyeing with hexamethyl phosphoric acid triamide and chlorinated ethylene solution of disperse dye Expired - Lifetime US3685955A (en)

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CH1819768 1968-12-05

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US (1) US3685955A (pl)
BE (1) BE742621A (pl)
DE (1) DE1959291C3 (pl)
FR (1) FR2025371B1 (pl)
GB (1) GB1262720A (pl)
NL (1) NL6918256A (pl)
PL (1) PL69790B1 (pl)
SU (1) SU394975A3 (pl)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111535051A (zh) * 2020-05-29 2020-08-14 西安工程大学 一种tpu型3d打印服装面料的染色方法
CN111549544A (zh) * 2020-05-29 2020-08-18 西安工程大学 一种abs型3d打印服装面料的染色方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1277881A (fr) * 1961-01-23 1961-12-01 Benckiser Gmbh Joh A Procédé de teinture de matières en polyacrylonitrile homopolymère
FR1277879A (fr) * 1961-01-23 1961-12-01 Benckiser Gmbh Joh A Procédé de teinture d'homopolymères d'acrylonitrile

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111535051A (zh) * 2020-05-29 2020-08-14 西安工程大学 一种tpu型3d打印服装面料的染色方法
CN111549544A (zh) * 2020-05-29 2020-08-18 西安工程大学 一种abs型3d打印服装面料的染色方法
CN111549544B (zh) * 2020-05-29 2023-04-07 西安工程大学 一种abs型3d打印服装面料的染色方法

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FR2025371A1 (pl) 1970-09-11
GB1262720A (en) 1972-02-02
DE1959291B2 (de) 1975-01-09
DE1959291C3 (de) 1975-08-14
DE1959291A1 (de) 1970-06-18
BE742621A (pl) 1970-06-04
PL69790B1 (pl) 1973-10-31
NL6918256A (pl) 1970-06-09
FR2025371B1 (pl) 1973-07-13
SU394975A3 (pl) 1973-08-22

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